Top Remote Senior Level Sales Leadership Jobs in Boston, MA

Lead the North America services go-to-market as the sales-facing professional services leader. Drive services positioning and attach rates, manage escalations, ensure high-quality value delivery, oversee at‑risk renewals, and represent PS in QBRs. Coach and develop teams, partner with sales on complex deals, and translate systemic issues into actionable improvement plans tied to commercial outcomes.

Own the SMB sales revenue target, pipeline coverage, forecasting, CRM discipline, and close rates. Build an AI-first sales motion, establish deal stages and reporting, hire and ramp at least two account executives, and coach the team on urgency, pipeline hygiene, qualification, and deal execution. Partner with Finance on forecasting and use data to improve win rates and conversion across the sales funnel.

Leads dealers across Central and Southern Alberta to achieve retail sales, market share, vehicle ordering, customer satisfaction, and accessory, service, OnStar, and leasing revenue goals. Develops district and dealer action plans, analyzes sales and market data, improves dealership performance, resolves customer issues, supports digital retail innovation, and builds dealer relationships. Requires frequent travel, independent work, cross-functional collaboration, and occasional extended hours.

Leads pre-sales professional services engagements, including scoping, proposals, quotes, statements of work, business cases, forecasting, and bookings. Partners with account executives, sales engineers, delivery teams, support, and resilience stakeholders to position services, conduct customer workshops, align scope with post-sale outcomes, and support larger deal closures. Requires expertise in change management, transformation, data protection, cloud, cyber resilience, and security. Travel is required up to 10%.

Lead Runpod’s Americas sales organization and revenue number across new business, expansion, and renewals. Manage and coach Account Executives and Account Managers, oversee forecasting and pipeline, lead complex enterprise deals and contract negotiations, build regional go-to-market strategy and sales playbooks, and convert product-led demand into revenue. Partner with Marketing, Product, Legal, and Finance while improving sales efficiency through AI and developing a remote-first team.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

Lead the US Higher Education sales team, coach sales excellence, build successful sales teams, and manage territory planning, assessment, and resource allocation. The role requires higher education leadership experience in software or SaaS, enterprise security familiarity, AI/ML understanding, and the ability to attract top sales talent and scale organizational processes.

Lead and scale a global team of Principal Agentic Technologists supporting strategic enterprise sales. Define technical sales methodologies, demonstrations, and proof-of-value frameworks for AI agent and non-human identity security products. Partner with sales, product, marketing, and engineering leaders to support major deals, influence product roadmaps, develop enablement programs, and communicate technical value to executives and architects.

Owns direct enterprise sales across a national territory of education employers, including universities, school districts, benefits pools, and associations. Manages prospecting, quotas, pipelines, and end-to-end RFP pursuits involving consultants, procurement, finalist presentations, and governance approvals. Builds strategic relationships with education benefits consultants, pool administrators, and benefits directors while communicating competitive value propositions. Requires deep health benefits and education-sector sales expertise, enterprise selling experience, data literacy, and sales process development skills.

Responsible for leading a sales team to develop and execute account strategies for Cloud Security, drive revenue growth, and manage relationships with major clients.